Hydrochloric Acid → HCID 22034125, compound

HRID 2121610Notes

Reaction equation

HRID 2121610 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9](=O)[C:10](=[N:18]O)[C:11](=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13].Cl.[CH3:22][NH:23][NH2:24]>CO>[NH2:18][C:10]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:24][N:23]([CH3:22])[C:9]=1[C:3]1[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=1[Cl:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6061MethylhydrazineHCID 178473115HCID 178473115, compound

Product 1

HCID 22034125HCID 22034125, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 4-(2,6-dichlorophenyl)-3-(hydroxyimino)-2,4-dioxobutanoate (14 g, 44 mmol) in MeOH (400 mL) at 0° C., add dropwise concentrated HCl (10 mL) followed by methyl hydrazine (2.02 g, 44 mmol). Stir the reaction mixture at ambient temperature for 8 h and concentrate in vacuo. Partition the residue between EtOAc (400 mL) and saturated aqueous NaHCO3 (150 mL) and separate the layers. Add water (200 mL) to the organic layer, followed by sodium hydrosulfite (150 g) and stir the resulting mixture vigorously for 4 h. Separate the organic phase, wash with water (200 mL), brine (200 mL), dry over MgSO4 and evaporate to obtain the title compound.

Workup

  1. concentrationconcentrate in vacuo
  2. customPartition the residue between EtOAc (400 mL) and saturated aqueous NaHCO3 (150 mL)
  3. customseparate the layers
  4. stirringstir the resulting mixture vigorously for 4 h
  5. customSeparate the organic phase
  6. washwash with water (200 mL), brine (200 mL)
  7. dry with materialdry over MgSO4
  8. customevaporate

Sources & evidence

ORD record
ord-f1fbef8a19de48c9beca6d31bad04c2c
Source dataset
uspto-grants-2004_02
Patent number
US06696445B2

Reaction notes

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